Question

Consider the molecule 1-tert-butyl-3-methylcyclohexane. These two groups can be cis or trans. Which arrangement is more stable? Answer this question by changing the bonds on the ring to wedges and/or dashes to show the proper spatial arrangement of the groups.

Answer 1

The first conformer cis-isomer (Picture 1) has both substituents in equatorial positions. Other conformer (on the right) has both substituents in axial positions. The conformer with both substituents in equatorial positions is more stable.  

Trans isomers have one substituent in an equatorial position and the other in an axial position (Picture 2). The conformer with the tert-butyl group in the equatorial position is more stable because tert-butyl group is larger.